What does it take to make the bold switch from a successful career in comms to venture investing? We sit down with Ashley Mayer to find out why and how she made her career transition. We talk about those early Twitter days—when social media was still uncharted territory—and how Ashley helped her then-CEO build a voice online while simultaneously growing her own presence. She even revisits that unforgettable “AirPod subway rescue” moment, a reminder of how randomness and relatability can shape what resonates online.

We dig into the art of storytelling in both media and business. Ashley makes a compelling case for why founders should prioritize narrative clarity and strategic intent over the allure of personal branding or chasing viral fame. It's about substance, not just splash. Ashley also opens up about the challenges of early-stage investing—from evaluating founders’ visions to navigating uncertainty—and shares how she made the leap from communications to venture capital. Her reflections on timing, serendipity, and career evolution are refreshingly candid.

And of course, we get into her latest venture: the podcast Great Chat. Ashley gives us a behind-the-scenes look at what it takes to build something authentic from the ground up—why experimentation matters, how to stay patient, and what it really means to engage with an audience. Join us for a thoughtful and inspiring conversation about tech, media, and building with intention.

About Ashley Mayer

Ashley Mayer is the cofounder and GP of Coalition Operators, where she and her partners back early-stage founders. She began her career at enterprise software company Box, where she led global communications from a 50-person startup through IPO. She then moved to Social Capital, where she led all things marketing and communications for three years, helping to launch new capital products and working with founders spanning healthcare, aerospace, climate, fintech, enterprise and education. Most recently, she led communications at a New York-based beauty company, Glossier.

Ashley has also been a key advisor to Mixing Board since before its official inception and serves on the organization’s operating council.

Sponsored by:
Delve.

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Learn more at delve.news/shift

Resources discussed in this episode:

• Box
• Glossier
• Great Chat podcast
• Chat GPT - Open AI
• Brian Johnson - New York Times article
• Magentic
• Platformer
• Hard Fork podcast
• Lingo
• Aura

Contact Allison Braley and Sean Garrett:

• MixingBoard.co
• LinkedIn: Allison Braley
• LinkedIn: Sean Garrett
• LinkedIn: Mixing Board
  
  

Contact Ashley Mayer:

• Website: coalitionoperators.com
• X: @ashleymayer
• LinkedIn: Ashley Mayer